Oh Holly Madison. I can’t quit you, even though I REALLY wanted to after reading The Vegas Diaries and couldn’t stand to hear one more second of your victimhood. But then my sweet sister-in-law gave me this book for my birthday and I realized maybe I just didn’t care that much about Holly’s life post-mansion, but I LOVE LOVE LOVE a good tell-all! So hold on to your hats, kids. This one is a doozy!
As a child, Holly was obsessed with Marilyn Monroe after her aunt gave her a set of paper dolls of the starlet and thus began Holly’s much-documented infatuation with all things old-Hollywood. Holly grew up in small-town Oregon and rural Alaska, but dreamed of one day being an actress. One day, while attending college at Portland State, Holly saw and advertisement for a “Millennium Playmate” contest that Playboy was putting on. Immediately, Holly signed up, even though she still had a flat chest and didn’t even own a bikini at that point. Holly seems to be REALLY dead set on proving to us that she was NOT a bimbo, Pamela Anderson wannabe from birth, talking about how she was always on the outside of social groups and had unique interests and hobbies. But it seems odd to me that she would be SO set on getting herself into Playboy and cool with posing naked if she didn’t even own a two-piece swimsuit?
Holly doesn’t win the contest, and this finally pushes her into getting breast implants. After maxing out three credit cards for the surgery, Holly finally makes her way down the coast to Los Angeles to start trying to achieve her dreams. She starts attending college but between that and her boob job, homegirl needed some money stat! So she did what every red-blooded American girl does and gets a job at Hooters!
All roads lead to the Playboy mansion, so this opportunity actually brought Holly to Hef. After working as a Hawaiian Tropics bikini model, as one does, Holly was approached by an old dude at an event who asks her if she wants to attend a Playboy party, to which Holly squeals “OF COURSE!” One of her friends tells her that the guys is actually Hugh Hefner’s private physician. Slash pimp, I guess. This mostly just makes me think my doctor ain’t doing enough for me. Where is my collection of men you found at a bikini contest, Dr. Johnson? WHERE?
So Holly goes to the party and then starts regularly hanging out at the Playboy fun-in-the-sun (so many hyphens! and hymens. Gross) parties. She never really interacted with Hef too much, but one of his seven girlfriends, a woman Holly calls Vicki, shows an interest in Holly and is very nice to her. At the same time, Holly’s roommate (whom she calls one of her two closest friends in LA) DARES to tell Holly that she is going to move in with her brother so rent will be covered. You guys? Holly had NO OTHER CHOICE than to try to move into the Playboy mansion. NO OTHER CHOICE. She couldn’t possibly have found another roommate or a different apartment! This was Los Angeles! They don’t have those there! So Holly’s horrible bitch of a roommate (this is the beginning of Holly showing time and time again that she has no idea how friendship works) basically sold her to Hef. Vicki helps arrange for Holly to come out with the whole Playboy posse one night to a nightclub (Le Deux, omg i feel like doing lines with Tara Reid of a Vn Dutch trucker hat) and Holly gets SO SO SO drunk yet somehow remembers the entire night with perfect clarity.
After da club, drunkass Holly goes back to the mansion and, unlike everything Vicki and the other girlfriends had been telling her, she was REQUIRED to participate in the bedroom orgy that awaited them. Holly does so reluctantly, and has sex with Hef for approximately 30 seconds before he moved on to the next girl. This all sounds SO AWFUL omg. So gross. After all of this, Holly is mortified and ashamed and then immediately asks Hef if she can move in as she has nowhere else to go. He agrees, telling her they could “try it out to see how it goes.” Holly accepts this and promptly prepares to move into the giant whorehouse and everything that would come with her new life…